USPTO Patents Application 09965610

Applicant
Serial No.
Filed
Page

Adam S. Cantor et al.
09/965,610
September 26, 2001
2 of 13

Attorney's Docket No.: 19426-0002001 / 56032US022

Amendments to the Claims:
This listing of claims replaces all prior versions and listings of claims in the application:

Listing of Claims :

1 . (Currently amended) A transdermal drug delivery composition comprising consisting
essentially of :

(a) a copolymer comprising

(i) one or more A monomers selected from the group consisting of alkyl acrylates

containing 4 to 12 carbon atoms in the alkyl group and alkyl methacrylates containing 4 to 12
carbon atoms in the alkyl group; and

(ii) one or more ethyl enically unsaturated B monomers copolymerizable with the

A monomer; and

(b) about 8% to about 30% by weight fentanyl based on the total weight of the
composition; and, optionally,

(c) a component selected from the group consisting of delivery enhancing adjuvants,
tackifiers, plasticizers, and combinations thereof,

wherein the composition is free of undissolved fentanyl.

2. (Original) The composition of claim 1 wherein the A monomer is selected from the group
consisting of isooctyl acrylate, 2-ethylhexyl acrylate, butyl acrylate, and cyclohexyl acrylate.

3. (Original) The composition of claim 1 wherein the A monomer is isooctyl acrylate.

4. (Original) The composition of claim 1 wherein the B monomer is selected from the group
consisting of 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, glyceryl acrylate, N,N-

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Attorney's Docket No.: 19426-0002001 / 56032US022

diethylacrylamide, 2-ethoxyethoxyethyl acrylate, 2-ethoxyethyl acrylate, tetrahydrofurfuryl
acrylate, acrylic acid, acrylamide, vinyl acetate, N-vinyl pyrrolidone and mixtures thereof.

5. (Original) The composition of claim 1 wherein the B monomer is 2-hydroxyethyl acrylate.

6. (Original) The composition of claim 5 wherein the copolymer comprises from about 5% to
about 45% of 2-hydroxyethyl acrylate by weight based on the total weight of all monomers in the
copolymer.

7. (Original) The composition of claim 1 wherein the copolymer further comprises a
macromonomer.

8. (Original) The composition of claim 7 wherein the macromonomer is a functionally
terminated polymethylmethacrylate.

9. (Original) The composition of claim 7 wherein the copolymer contains from about 1% to
about 6% of macromonomer by weight based on the total weight of all monomers in the
copolymer.

10-15. (Canceled).

16. (Original) The composition of claim 1 wherein the concentration of fentanyl in said
transdermal drug delivery composition is from about 12% to about 24% by weight.

17. (Original) The composition of claim 7 wherein the copolymer comprises from about 50 to
about 94%) isooctyl acrylate, about 5% to about 40%> 2-hydroxyethyl acrylate, about 1% to about
6%> macromonomer, and 0% to about 20% vinyl acetate by weight.

Applicant : Adam S. Cantor et al. Attorney's Docket No.: 19426-0002001 / 56032US022

Serial No. : 09/965,610

Filed : September 26, 2001

Page : 4 of 13

18. (Original) The composition of claim 7 wherein the copolymer comprises from about 52% to
about 60% isooctyl acrylate, about 35% to about 40% 2-hydroxyethyl acrylate, about 1% to
about 4%> macromonomer, and 0% to about 10% vinyl acetate by weight.

19-27. (Canceled).

28. (Original) A method of treating in a mammal a condition capable of treatment by fentanyl
comprising the steps of:

(a) providing a composition according to claim 1 ;

(b) placing the composition on the skin of a mammal; and

(c) allowing the composition to remain on the skin for a time sufficient to establish or
maintain a therapeutically effective blood level of fentanyl in the mammal.

29. (Original) A method of providing analgesia to a mammal comprising the steps of:

(a) providing a composition according to claim 1 ;

(b) placing the composition on the skin of a mammal; and

(c) placing the composition to remain on the skin for a time sufficient to establish or
maintain an analgesically effective blood level of fentanyl in the mammal.

30-34. (Canceled).

35. (Currently amended) A transdermal drug delivery composition comprising consisting
essentially of :

(a) a copolymer comprising:

(i) one or more A monomers selected from the group consisting of isooctyl
acrylate, 2-ethylhexyl acrylate, butyl acrylate, and cyclohexyl acrylate; and

(ii) one or more ethyl enically unsaturated B monomers copolymerizable with the
A monomer; wherein the B monomers are selected from the group consisting of 2-hydroxyethyl

Applicant : Adam S. Cantor et al. Attorney's Docket No.: 19426-0002001 / 56032US022

Serial No. : 09/965,610

Filed : September 26, 2001

Page : 5 of 13

acrylate, 2-hydroxyethyl methacrylate, glyceryl acrylate, N,N-diethylacrylamide, 2-
ethoxyethoxyethyl acrylate, 2-ethoxyethyl acrylate, tetrahydrofurfuryl acrylate, acrylic acid,
acrylamide, vinyl acetate, N-vinyl pyrrolidone and mixtures thereof; and

(b) about 8% to about 30% by weight fentanyl based on the total weight of the
composition; and, optionally,

(c) a component selected from the group consisting of delivery enhancing adjuvants,
tackifiers, plasticizers, and combinations thereof,

wherein the composition is free of undissolved fentanyl.

36. (Currently amended) A transdermal drug delivery composition comprising consisting
essentially of :

(a) a copolymer comprising:

(i) one or more A monomers selected from the group consisting of isooctyl
acrylate, 2-ethylhexyl acrylate, butyl acrylate, and cyclohexyl acrylate; and

(ii) about 5% to about 45% of one or more ethylenically unsaturated B monomers
copolymerizable with the A monomer; wherein the B monomers are selected from the group
consisting of 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, glyceryl acrylate, N,N-
diethylacrylamide, 2-ethoxyethoxyethyl acrylate, 2-ethoxyethyl acrylate, tetrahydrofurfuryl
acrylate, acrylic acid, acrylamide, vinyl acetate, N-vinyl pyrrolidone and mixtures thereof; and

(b) about 8%> to about 30%> by weight fentanyl based on the total weight of the
composition; and, optionally,

(c) a component selected from the group consisting of delivery enhancing adjuvants,
tackifiers, plasticizers, and combinations thereof,

wherein the composition is free of undissolved fentanyl.

37-38. (Canceled).

Applicant : Adam S. Cantor et al. Attorney's Docket No.: 19426-0002001 / 56032US022

Serial No. : 09/965,610

Filed : September 26, 2001

Page : 6 of 13

39. (Currently amended). The composition of claim 1 wherein the composition further
comprises contains a delivery enhancing adjuvant.

40. (Previously presented). The composition of claim 39 wherein the delivery enhancing
adjuvant is selected from the group consisting of alkane polyols, fatty acids, fatty acid esters,
fatty alcohols, terpenes, C 5 -Cig alkyl esters of a carboxylic acid, and mixtures thereof.

41 . (Previously presented). The composition of claim 39 wherein the delivery enhancing
adjuvant is selected from the group consisting of ethyl oleate, isopropyl myristate, glycerol,
tetraglycol, methyl laurate, N,N-dimethyldodecylamine N-oxide, limonene, terpineol,
tetraethylene glycol, menthol, and mixtures thereof.

42. (Previously presented). The composition of claim 39 wherein the concentration of the
delivery enhancing adjuvant is from about 5% to about 40% by weight based on the total weight
of the composition.

43. (Currently amended). The composition of claim 39 wherein the skin permeation enhancer
delivery enhancing adjuvant is tetraglycol.

44. (Currently amended). The composition of claim 39 wherein the skin permeation enhancer
delivery enhancing adjuvant is methyl laurate.

45. (Currently amended). The composition of claim 17 wherein the concentration of fentanyl is
from about 12% to about 22% by weight, and wherein the composition further comprises
contains about 15% to about 35% by weight of a permeation enhancer delivery enhancing
adjuvant selected from the group consisting of methyl laurate, tetraglycol, and mixtures thereof.

Applicant : Adam S. Cantor et al. Attorney's Docket No.: 19426-0002001 / 56032US022

Serial No. : 09/965,610

Filed : September 26, 2001

Page : 7 of 13

46. (Previously presented). The composition of claim 45 wherein the concentration of fentanyl is
from about 12% to about 17% by weight and the concentration of methyl laurate is from about
20% to about 35% by weight.

47. (Previously presented). The composition of claim 45 wherein the concentration of fentanyl is
from about 15% to about 22% by weight and the concentration of tetraglycol is from about 15%
to about 25% by weight.

48-51. (Withdrawn).

52. (Previously presented). A device for the transdermal delivery of fentanyl comprising a
backing and a composition according to claim 1 , said composition being adhered to one surface
of the backing.

53. (Previously presented). The composition of claim 39 wherein the delivery enhancing
adjuvant is a skin permeation enhancer.

54. (Currently amended). A transdermal drug delivery composition comprising consisting
essentially of:

(a) a copolymer comprising

(i) one or more A monomers selected from the group consisting of isooctyl
acrylate, 2-ethylhexyl acrylate, butyl acrylate, and cyclohexyl acrylate; and

(ii) about 5% to about 45% of one or more ethylenically unsaturated B monomers
copolymerizable with the A monomer; wherein at least one B monomer is 2-hydroxyethyl
acrylate; and

(b) about 8%> to about 30% by weight fentanyl based on the total weight of the
composition; and

Applicant : Adam S. Cantor et al. Attorney's Docket No.: 19426-0002001 / 56032US022

Serial No. : 09/965,610

Filed : September 26, 2001

Page : 8 of 13

(c) a delivery enhancing adjuvant selected from the group consisting of methyl laurate,
tetraglycol, and mixtures thereof;

wherein the composition is substantially free of undissolved fentanyl.

55-91. (Withdrawn).

92. (Currently amended) A device for the transdermal drug delivery of fentanyl comprising a
backing and a pressure sensitive adhesive composition adhered to one surface of the backing,
the composition comprising consisting essentially of :

(a) a copolymer comprising

(i) one or more A monomers selected from the group consisting of alkyl acrylates
containing 4 to 12 carbon atoms in the alkyl group and alkyl methacrylates containing 4 to 12
carbon atoms in the alkyl group; and

(ii) one or more ethyl enically unsaturated B monomers copolymerizable with the
A monomer; and

(b) about 8% to about 30% by weight fentanyl based on the total weight of the
composition;

wherein the composition is free of undissolved fentanyl.

93. (Currently amended) A device according to claim 92, wherein the composition comprises
about 8% fentanyl based on the total weight of the composition concentration of fentanyl in said
composition is about 8% by weight .

94. (New) A device for the transdermal delivery of fentanyl comprising a backing and a
composition according to claim 92, said composition being adhered to one surface of the
backing.

95. (New) A transdermal drug delivery composition consisting essentially of:

Applicant : Adam S. Cantor et al. Attorney's Docket No.: 19426-0002001 / 56032US022

Serial No. : 09/965,610

Filed : September 26, 2001

Page : 9 of 13

(a) a copolymer of:

(i) one or more A monomers selected from the group consisting of isooctyl
acrylate, 2-ethylhexyl acrylate, butyl acrylate, and cyclohexylacrylate; and

(ii) one or more ethyl enically unsaturated B monomers copolymerizable with the
A monomer, wherein the B monomers are selected from the group consisting of 2 -hydroxy ethyl
acrylate, 2-hydroxymethacrylate, vinyl acetate, glycidyl methacrylate, and mixtures thereof; and

(b) about 8% to about 30% by weight fentanyl based on the total weight of the
composition;

wherein the composition is free of undissolved fentanyl.

96. (New) A composition according to claim 95, wherein the concentration of fentanyl in said
composition is about 8% by weight.

97. (New) A device for the transdermal delivery of fentanyl comprising a backing and a
composition according to claim 95, said composition being adhered to one surface of the
backing.

98. (New) A transdermal drug delivery composition consisting essentially of:

(a) a copolymer comprising

(i) about 40 to about 95% by weight of one or more A monomers selected from
the group consisting of alkyl acrylates containing 4 to 12 carbon atoms in the alkyl group and
alkyl methacrylates containing 4 to 12 carbon atoms in the alkyl group;

(ii) about 5 to about 55% by weight of one or more ethylenically unsaturated B
monomers copolymerizable with the A monomer; and

(iii) 0 to about 20% by weight of one or more macromonomers copolymerizable
with the A and B monomers;

(b) about 8%> to about 30% by weight fentanyl based on the total weight of the
composition; and, optionally,

Applicant
Serial No.
Filed
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Adam S. Cantor et al.
09/965,610
September 26, 2001
10 of 13

Attorney's Docket No.: 19426-0002001 / 56032US022

(c) a component selected from the group consisting of delivery enhancing adjuvants,
tackifiers, plasticizers, and combinations thereof,

wherein the composition is free of undissolved fentanyl.

99. (New) A composition according to claim 98, wherein the concentration of fentanyl in said
composition is about 8% by weight.

100. (New) A composition according to claim 98, wherein the copolymer contains from about
1% to about 6% of the macromonomer by weight based on the total weight of all monomers in
the copolymer.

101. (New) A composition according to claim 98, wherein the composition includes a delivery
enhancing adjuvant.

102. (New) A composition according to claim 101, wherein the delivery enhancing adjuvant is
selected from the group consisting of methyl laurate, isopropyl myristate, and mixtures thereof.

103. (New) A device for the transdermal delivery of fentanyl comprising a backing and a
composition according to claim 98, said composition being adhered to one surface of the
backing.